A series of bis-compounds (2) were synthesized by condensing dihydro-1,3-(disubstituted)phenyl-2-thioxopyrimidine-4,6(1H,5H)-dione with hippuric acid in presence of acetic anhydride. The compound (2) on further treatment with aromatic amine afforded dihydropyrimidine (3) through an eco-friendly procedure by sonication. The sonication method reduces time and gives higher yields, and also the effluent produced is free from hazardous contamination and organic by-products. The novel pyrimidines were also synthesized by traditional methods for comparison purposes and sonication method was found to be superior. Structures of the synthesized compounds have been elucidated on the basis of elemental analysis and spectral data.
New potent antibacterials, fused isoxazole and pyrazole derivatives, were synthesized using 5,5-dimethylcyclohexane-1,3-dione (1) and 3-[(4-chlorobenzylidene) amino]-2-thioxoimidazolidin-4-one (2) as synthons. Aromatic aldehydes on condensation with 1 and 2 gave 2-arylidene-5,5-dimethylcyclohexane- 1,3-dione (3) and 5-arylidene-3-[(4-chlorobenzylidene)amino]-2-thioxoimidazolidin-4-one (4), respectively. Compounds 3 and 4 were forced to undergo heterocyclization reaction with nucleophilic reagents to give the title compounds. The newly synthesized heterocyles (5-8) were characterized based on their chemical properties and spectroscopic data, and were found to inhibit Staphylococcus aureus and Corynebacterium diphtheriae.
magnified imageA new series of bis‐1,5‐[2′H,3′H‐dihydro‐4′(substituted phenyl)‐1′,5′‐benzothiazipin‐2′‐oxy]‐3,3‐dimethyl‐1,4‐cyclohexadiene 3 and bis‐1,5‐[‐2′,3′,4′,5′‐teterahydro‐2′‐(substitutedphenyl)‐4′‐oxothiophen‐3′‐carboxylate]‐3,3‐dimethyl‐1,4‐cyclohexadiene 4 have been synthesized by reacting 1,3‐bis‐[substituted cinnamate]‐3,3‐dimethyl‐1,4‐cyclohexadiene 2 with 2‐aminothiophenol and thiogylcolic acid, respectively, through an environmentally benign procedure. The title compounds have been evaluated for their antimicrobial activities. Reaction under ultrasound irradiation resulted in enhancement of yields and reaction rates. Structures of the synthesized compounds have been elucidated on the basis of the elemental analysis and spectral data. J. Heterocyclic Chem., (2009).
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